Well, December is finally here in Chicago. And with the polar vortex making its appearance this year, summer seems like a distant memory already.
But here at The Ben Lalez Team, we refuse to let winter dictate how much fun we have during the winter months. We’ve written a lot about winter activities in the city, holiday markets, and events in Chicago. But sometimes you just need to get out of town for a bit.
That’s why this week, we spent some time looking up local getaways that can bring you romance, relaxation, and a bit of adventure. We’re talking about places where someone else makes the bed for a change, and where dinner reservations are already handled, so you don’t have to have ‘that discussion’ again.
So if you’re looking to get away with your significant other (without the kids), here are some of the best spots for couples within a 3-hour drive of Chicago!
Goldmoor Inn in Galena, Illinois
Goldmoor Inn is 3 hours from Chicago, located above the Mississippi River, with just 13 suites in total. Each suite has its own fireplace, whirlpool tub, and king bed, all decorated differently.
Edge is their on-site restaurant and focuses on farm-to-table ingredients. If you’re there in December, they arrange scenic horse-drawn sleigh rides through the area.
After dinner, you can drink the complimentary wine in your room or book an in-room couples’ massage for around $125 per person.
Every stay includes breakfast in the morning and dessert in the evening. Rates typically start at $350-$400 per night in winter and includes food.
With only 13 suites on the property, it’s very intimate and cozy. The staff specializes in celebrations, so if you’re doing an anniversary or engagement, be sure to let them know!
Click here to check their packages and events.
Jail Hill Inn in Galena, Illinois
This place was rated the #1 B&B in the United States in TripAdvisor’s Travelers’ Choice Awards.
Jail Hill Inn is housed in a 135-year-old brick jail converted into luxury accommodations. The property has six suites, each over 800 square feet, with whirlpool tubs, fireplaces, king beds, and heated bathroom floors.
They can arrange in-room massages for both of you, or add flowers and custom cakes if you’re celebrating something. In winter, they’ll provide sleds if you want to enjoy some time in the snow.
If you’re looking to stay here on the weekends, expect to pay around $300 – $450 per night. Rates are lower if you can make it out during the week, and you can click here to check availability and prices. Given that breakfast, evening wine and food, and extras are included, we think it’s worth the price.
Inn at Irish Hollow in Galena Countryside, Illinois
Just outside Galena, you’ll find the Inn at Irish Hollow sitting on 500 acres. You can stay in the historic main inn or book one of five private cottages. Each cottage comes equipped with a wood-burning fireplace, a king bed, and a double whirlpool tub.
Every morning, a full country gourmet breakfast gets delivered to your cottage door or served in the 19th-century General Store dining room.
Irish Hollow offers several holiday packages and winter packages for couples. The Winter Fireside package bundles two or three nights with breakfast each morning and a multi-course candlelight dinner one night, plus champagne and handmade chocolates. There’s a Christmastime special running through December and January that adds an Olde World Christmas dinner and a full country gourmet breakfast each morning.
The inn rooms start around $225 – $275 per night, with private cottages running $300 – $400 in the winter. Irish Hollow is often called Illinois’s most romantic B&B and is located about three hours away from Chicago.
Lazy Cloud Bed & Breakfast in Lake Geneva, Wisconsin
If you can make it out to Lake Geneva, Lazy Cloud is worth checking out.
They have two locations near Lake Geneva, both dedicated to couples. All the suites come with double whirlpool tubs right in the room, wood-burning fireplaces, and queen or king beds. Each suite has its own private entrance and outdoor sitting area.
They have a few packages to choose from. The Romantic Escape Package costs $175 and includes a picnic dinner basket for two, a dozen roses, Lazy Cloud T-shirts and mugs, handmade chocolates, and breakfast in bed one morning. The Sweetheart Special is simpler at $85 with flowers, a couple’s conversation game, a romance book, and chocolates.
If you’re looking to stay there this winter, it’ll cost around $150 – $280 per night, depending on the day and which suite you book. Since wine, dessert, and other perks are already included in the base price, it’s a decent value.
It’s been called the #1 Couples’ Getaway in the Lake Geneva area, and we think it’s a great place to spend a night or two.
SevenOaks in Lake Geneva, Wisconsin
SevenOaks has been rated the #1 B&B in Lake Geneva, and is a boutique bed-and-breakfast with nine cottage suites just minutes from Lake Geneva’s downtown.
Inside each private cottage, you’ll find a two-person spa tub, heated bathroom floors and towel warmers, a fireplace, and a small kitchenette.
Every morning, a continental breakfast basket gets delivered to your cottage at whatever time you request. In the afternoon, the inn hosts a complimentary wine and cheese welcome reception, or they’ll often just leave a bottle of wine and snacks in your room.
If you want to go mid-week, SevenOaks runs a fall and winter special offering $20 off two-night stays for Sunday through Thursday arrivals from November through May in select cottages.
To find out more information about SevenOaks, visit their website.
Serenity Springs in Michigan City/La Porte, Indiana
Serenity Springs is a couples-only resort about an hour east of Chicago with over 30 private cabins on 85 wooded acres.
All cabins come with a two-person sunken whirlpool tub, a gas log fireplace, a king bed, and a private deck. You can spend your entire stay in a robe without seeing anyone, thanks to their butler door system.
The butler door is one of the best features here. Staff delivers items like your breakfast basket, snacks, or firewood to a two-way cabinet, and a light indicates when something’s there. You retrieve it from inside without opening your front door. You really don’t ever have to leave your room or open a door!
In winter, couples can walk the private trails or borrow complimentary ice skates for the pond when it freezes. On weekends the resort offers horse-drawn carriage rides. Many cabins have an outdoor fire pit with wood and roasting sticks provided.
Click here to check their rates and packages. They often run seasonal deals. We suggest budgeting around $700 – $900 for a romantic two-night weekend.
From Chicago, it’ll take you around 90 minutes to get there.
Castle in the Country in Allegan, Michigan
Castle in the Country is a luxury bed-and-breakfast on a 65-acre estate, around 2.5 – 3 hours from Chicago. The property has two buildings, a 1906 Victorian “Castle” with five rooms and the “Castle Keep” next door with five spacious modern suites. You’ll be surrounded by wooded trails for snowshoeing, a private lake with a gazebo, and outdoor bonfire pits.
Most rooms have whirlpool tubs for two, gas fireplaces, and king beds. They also have an on-site spa room where you can book side-by-side couples’ massages, often included in packages.
Every stay includes a two-course gourmet breakfast each morning with local Michigan ingredients. In winter, they often serve breakfast in bed for the suites, and offer private dinners for guests on certain nights.
There are two packages to choose from, both offering accommodations, dining, and massages. The innkeepers are a husband-and-wife team known for their personal touch, so we know you’ll enjoy your stay.
Wickwood Inn in Saugatuck, Michigan
Wickwood Inn is an 11-room boutique bed-and-breakfast about 2.5 hours from Chicago. The inn is housed in a colonial-style 1937 mansion. Each room is decorated uniquely with antique furnishings and original artwork.
Food is a highlight here. The inn’s owner is a renowned cookbook author. In the morning, you get a gourmet breakfast with dishes sourced from local farms and markets. In the evening, Wickwood offers a complimentary “Sips & Small Plates” hour in the library with charcuterie, artisanal cheeses, and wines.
While Wickwood doesn’t have jetted tubs or fireplaces in individual rooms, they make sure you’re comfortable with plush down comforters, high-end linens, and spa robes. The staff pays attention to celebrating romantic milestones.
They have some fantastic seasonal offerings going on right now, so make sure to check their website for what’s available.
Wickwood Inn was featured in Midwest Living’s list of romantic winter getaways, so we’re sure you’ll have a wonderful experience here.
Final Thoughts
So there you have it. Eight different spots within a three-hour drive of Chicago, each offering something a little different for couples looking to get away this winter.
At The Ben Lalez Team, we know that finding the right home in Chicago is important. But so is knowing when to leave it for a bit. If you’re looking for recommendations on romantic neighborhoods in the city, weekend getaway ideas, or anything else Chicago-related, we’re always happy to help. Just give us a shout and let’s connect!
Stay warm out there, and enjoy your winter escape.
